Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1989-12-19
1991-01-15
Lee, Mary C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514400, 548336, 548346, A61K 31415, C07D40300, C07D23354
Patent
active
049854402
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new imidazol-2-yl-derivatives of bicyclic compounds, in particular to imidazol-2-yl-derivatives of 3,4-dihydro-2H-1-benzopyran, 2H-1-benzopyran, 1,2,3,4-tetrahydronaphthalene and 1,2-dihydronaphthalene, to a process for their preparation and to pharmaceutical compositions containing them.
The invention provides compounds having the following general formula (I) ##STR2## wherein the symbol represents a single or double bond; alkyl; alkyl such as C.sub.1 -C.sub.6 alkyl;
The invention also includes within its scope all the possible isomers, stereoisomers and their mixtures and the metabolites and the metabolic precursors or bio-precursors of the compounds of formula (I).
Pharmaceutically acceptable salts of the compounds of formula (I) include acid addition salts, with inorganic, e.g. nitric, hydrochloric, hydrobromic, sulphuric, perchloric and phosphoric, acids or organic, e.g. acetic, propionic, glycolic, lactic, oxalic, malonic, malic, maleic, tartaric, citric, benzoic, cinnamic, mandelic, fumaric, methanesulfonic and salicyclic acids, and salts with inorganic, e.g. alkali metal, especially sodium or potassium, bases or alkaline-earth metal, especially calcium or magnesium, or with organic bases, e.g. alkylamines, preferably triethylamine, or basic naturally occurring aminoacids, preferably arginine.
The alkyl groups may be branched or straight chain groups.
A C.sub.1 -C.sub.8 alkyl group is e.g. a C.sub.1 -C.sub.6 alkyl group such as a C.sub.1 -C.sub.3 alkyl group. In particular it may be methyl, propyl, butyl or hexyl.
A C.sub.1 -C.sub.4 alkyl group is preferably methyl, ethyl, propyl, isopropyl or butyl, in particular methyl or ethyl.
As stated above the present invention also includes within its scope pharmaceutically acceptable bio-precursors (otherwise known as pro-drugs) of the compounds of formula (I), i.e. compounds which have a different formula to formula (I) above but which nevertheless upon administration to a human being are converted directly or indirectly in vivo into a compound of formula (I).
Preferred compounds of the invention are the compounds of formula (I) as defined above, wherein alkyl;
Specific examples of preferred compounds according to the present invention are: 2-[3-(1-methyl-1H-imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2-methylpropanoa te; -imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2-methylpropanoate; 5-[3-(1-methyl-1H-imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2,2-dimethylpent anoate; -imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2,2-dimethylpentanoate; 5-[3-(1-methyl-1H-imidazol-2-yl)-2-n-propyl-2H-1-benzopyran-6-yl]oxy-2,2-d imethylpentanoate; 5-[3-(1-methyl-1H-imidazol-2-yl)-2-i-propyl-2H-1-benzopyran-6-yl]oxy-2,2-d imethylpentanoate; -imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2,2-dimethylpentanoate; -imidazol-2-yl)-2H-1-benzopyran-6-yl]oxy-2,2-dimethylpentanoate; (.+-.)-5-[3,4-dihydro-2,3-cis-3-(1-methyl-1H-imidazol-2-yl)-2-n-propyl-2H- 1-benzopyran-6-yl]oxy-2,2-dimethylpentanoate; 5-[5,6-dihydro-7-(1-methyl-1H-imidazol-2-yl)naphthalen-2-yl]oxy-2,2-dimeth ylpentanoate; 5-[5,6-dihydro-6-methyl-7-(1-methyl-1H-imidazol-2-yl)naphthalen-2-yl]oxy-2 ,2-dimethylpentanoate; 5-[5,6,7,8-tetrahydro-7-(1-methyl-1H-imidazol-2-yl)naphthalen-2-yl]oxy-2,2 -dimethylpentanoate; acid; thylpentanoic acid;
The compounds of the invention and the salts thereof can be obtained by a process comprising ##STR3## wherein the symbol , Z, R.sub.2 and R.sub.3 are as defined above, with a compound of formula (III) ##STR4## wherein X is an halogen atom or the residue of an active ester group and R, R.sub.1 and n are as defined above; or chloroform, in the presence of an alkali metal hydroxide, so as to obtain a compound of formula (I) wherein n is zero, R is hydrogen, R.sub.1 is methyl and the symbol , Z, R.sub.2 and R.sub.3 are as defined above; and, if desired, converting a compound of formula (I) into another compound of formula (I), and/or, if desired, converting a compound of formula (I) into a salt thereof, and/or, if desired, converting a salt into a free compound, and/or, if de
REFERENCES:
Cozzi et al., Il Farmaco, vol. 42, fasc 3, 1986.
Cozzi et al., J. Med. Chem., 1986, 29; 404-410.
Carganico Germano
Chiari Augusto
Cozzi Paolo
Lovisolo Pierpaolo
Severino Dino
Farmitalia Carlo Erba S.r.l.
Lee Mary C.
Whittenbaugh Robert C.
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